Chiefly consisting of family letters re business activities, the Civil War, economic hardships on the home front, devaluation of currency, and Reconstruction. Including letter, 12 Aug. 1863, Charleston, S.C., to Rosalie Raymond, re life with her grandmother, learning to read, sending sugar, and purchasing toys for her daughter while in town; letter, June 1865, New York, N.Y., to "My Dear Mother," Charleston, S.C., re family affairs, attacks by freed slaves and black military regiments, and financial losses in the region caused by the war. Letter, 15 Oct. 1867, New York, N.Y., to "My Dear Mother," re visiting friends and family, current affairs, and economic hardships; undated letter, from H.H. Raymond, re attack on Fort Sumter, purchasing children's toys, and shipping supplies from Charleston, S.C.